Is Your CS Career Future Proof?

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Hey CS Pro,

If it feels like the ground keeps shifting under your feet in customer success, you are not imagining it. AI, reorgs, layoffs, and tighter budgets are changing our jobs faster than most careers can keep up, and in 2026 no one is waiting for you to catch up.

This episode and newsletter are your straight talking playbook for how to protect and ELEVATE your CS career next year, so you stay relevant, visible, and commercially valuable.

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The old CS career ladder is gone

Let us be very real for a second. The past few years in customer success have had more downs than ups. People you know have been hit by layoffs, reorgs, or acquisitions that just did not land. CS is still too often treated as a support function instead of a growth function.

At the same time, AI is quietly (and not so quietly) replacing entire chunks of the work we used to do manually. Companies are hiring fewer people, CS budgets are tighter, titles are flattening, and if your role is not clearly tied to commercial value, it is at risk.

We have already lived through three clear eras of CS:

• Pre pandemic CS where the job was mostly about keeping customers happy, onboarded, and using the product.

• The growth at all costs era around 2020 to 2022, when teams were hiring like crazy and simply keeping up felt like enough.

• The AI era we are in now, where doing a solid job is just the baseline and companies expect faster response times, clearer value, and real revenue impact from CS.

In that old world, being the person who ticked all the boxes and ran all the QBRs could keep you safe. In 2026, that is not enough. Doing your job well is expected. What sets you apart is your ability to drive revenue, influence change, and adapt faster than the market shifts.

Here are three career mistakes I see over and over, that will quietly hold you back if you do not fix them:

1. Waiting for your company to define your growth. If you are relying on your manager to design your development plan, you are already behind. The most successful CS pros I know build their own path and then invite their manager into it, not the other way around.

2. Living in reactive work. If your week is mostly putting out fires, chasing customers for feedback, and doing tasks AI could easily handle, you are not building strategic value. You are making yourself replaceable.

3. Tying your value to tasks, not revenue. Counting calls, QBRs, or onboarded customers is not the same as showing how you protected retention or created expansion. Tasks are where AI wins. Outcomes are where YOU win.

Your future-proof playbook for 2026

Let us talk about what to do instead:

Become revenue fluent

Revenue is the language of business. If you work in a business, you need to speak it. Start asking yourself every single day:

What am I doing today that helps my company MAKE money or SAVE money

If you cannot answer that clearly, that is your first signal. Talk to your manager, your finance partner, your sales partner. Ask how renewal, expansion, and churn targets are set. Ask how your accounts roll up into NRR and GRR. Bring that lens into everything you do, from success plans to follow up emails.

Build your personal operating system

Do not wait for your company training calendar. Your career is YOUR project. You need your own toolkit that follows you to every future role.

That looks like:

• Time blocking at least a little protected time for strategic work each week, and treating that time as non negotiable.

• Creating AI prompts to handle repeat work, like call summaries, risk scans, or first draft emails, so you get time back for human conversations.

• Building and reusing your own templates for QBRs, value reviews, success plans, and renewal prep, across accounts and even across companies.

• Setting up a simple system to track wins and impact, so every retention save, expansion, and risk you mitigated is captured in one place.

Train AI to work for you, not replace you

If you see AI as the enemy, it will pass you by. I want you to treat AI like a personal assistant you are training. You are the pilot, AI is the co pilot.

You can use AI to:

• Draft success plans

• Prep for business reviews

• Scan accounts for renewal risk

• Brainstorm growth plays and talk tracks

But it only becomes powerful when you feed it your customer context, your value stories, your tone, your goals. The CS pros who will thrive in twenty twenty six are the ones who can say, I know how to train AI to extend my impact.

Document your impact and act like the next level you

Create your brag list or accomplishment tracker.

There are two big reasons to document your impact.

First, promotions. When I moved from CSM to VP in under seven years, it was not because I “felt ready.” It was because I could show a concrete record of revenue influence and business impact over time.

Second, mobility. Most of us stay at a company for maybe 18 to 36 months. Your career does not live and die at one logo. When you track your retention saves, expansion dollars, and key wins week by week, you are basically writing your resume as you go.

Use whatever tool works for you, from a spreadsheet to Notion. If you want help, my Customer Success Accomplishment Tracker gives you a ready made structure to capture wins, quantify impact, and turn it into promotion ready statements.

Start acting like the next level version of you.

If you want to be a senior CSM, start thinking, writing, and running calls like one now. If you want to be a VP, start presenting and making decisions through that lens.

Back in 2018, I was a director of CS at a startup. Things looked great on the surface, but the moment my CFO asked, How much revenue did your team drive this quarter and I did not have an answer, it woke me up.

From there, I rebuilt everything with revenue in mind. Success plans. Business reviews. Team KPIs. Weekly meetings. We started tracking NRR and GRR obsessively and talking openly about the revenue gap and how we would close it. My team became genuinely commercial, not just “customer friendly.”

The result? I was invited to board meetings, promoted faster, and treated like part of the go-to-market leadership, not a support function.

You can create that same shift in your own career, starting now.

Ready to turn your CS team into revenue-driving pros?

Most CS orgs don’t need another pep talk. They need practical training that actually shifts how they work.

That’s where I come in.

Whether you need your team to:

✔️ Handle renewals with confidence

✔️ Spot upsell opportunities

✔️ Run ROI-driven QBRs

✔️ Build scalable playbooks

… I’ve got you.

I’ve trained CS teams at Microsoft, Atlassian, Workiva, Flywire and more, giving their post-sale teams the playbooks they actually need to succeed in today’s economy.

If you’re planning your next offsite, team day, or kickoff event, now’s the time to book.

Let’s build a team of strategic CSMs (not firefighters).

📞 Book a call with me

👩‍🏫 View past workshops

2026 is around the corner. No one is coming to hand you a safe career path. It is your career, and you have full ownership. Start speaking revenue, build your personal operating system, train AI to be your co-pilot, and document the impact you are already creating.

Your future self will be very glad you did.

Have a listen to the latest podcast:

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika

PS - CSM RevUP Academy is currently full. Don't miss your shot at next time! Get the strategies, playbooks, and build your confidence into a revenue-generating CS Pro. Join the VIP Waitlist today to be first notified when the doors open again.